U.S. patent application number 16/675197 was filed with the patent office on 2020-05-07 for novel compound and organic electroluminescent device comprising the same.
The applicant listed for this patent is LG Display Co., Ltd. MATERIAL SCIENCE CO., LTD.. Invention is credited to Jeonghoe Heo, Sunghoon Kim, Sunjae Kim, Dong Hun Lee, Tae Wan Lee, Seong-Min Park, Inbum Song, Seunghee Yoon.
Application Number | 20200144509 16/675197 |
Document ID | / |
Family ID | 70459123 |
Filed Date | 2020-05-07 |
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United States Patent
Application |
20200144509 |
Kind Code |
A1 |
Song; Inbum ; et
al. |
May 7, 2020 |
NOVEL COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE
SAME
Abstract
Organic electroluminescent devices with lowered driving
voltages, and enhanced efficiencies and lifetimes are provided.
Inventors: |
Song; Inbum; (Seoul, KR)
; Yoon; Seunghee; (Seoul, KR) ; Kim; Sunghoon;
(Seoul, KR) ; Lee; Tae Wan; (Seoul, KR) ;
Lee; Dong Hun; (Seoul, KR) ; Heo; Jeonghoe;
(Seoul, KR) ; Park; Seong-Min; (Goyang-si, KR)
; Kim; Sunjae; (Seoul, KR) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
LG Display Co., Ltd.
MATERIAL SCIENCE CO., LTD. |
Seoul
Seoul |
|
KR
KR |
|
|
Family ID: |
70459123 |
Appl. No.: |
16/675197 |
Filed: |
November 5, 2019 |
Current U.S.
Class: |
1/1 |
Current CPC
Class: |
H01L 51/0058 20130101;
H01L 51/0061 20130101; H01L 51/56 20130101; C09K 11/06 20130101;
H01L 51/0059 20130101; H01L 51/5064 20130101; C09K 2211/10
20130101; H01L 29/7869 20130101; H01L 51/5012 20130101; H01L
51/5253 20130101; H01L 51/0052 20130101; H01L 51/006 20130101; H01L
51/001 20130101; H01L 27/3248 20130101; H01L 27/1225 20130101; H01L
51/5092 20130101; H01L 51/508 20130101; H01L 2251/558 20130101;
H01L 51/0072 20130101; H01L 51/5088 20130101; C07D 209/86
20130101 |
International
Class: |
H01L 51/00 20060101
H01L051/00; C07D 209/86 20060101 C07D209/86; C09K 11/06 20060101
C09K011/06 |
Foreign Application Data
Date |
Code |
Application Number |
Nov 5, 2018 |
KR |
10-2018-0134472 |
Oct 14, 2019 |
KR |
10-2019-0126903 |
Claims
1. A compound represented by the following Chemical Formula 1:
##STR00086## wherein Ar.sub.1 is represented by the following
Chemical Formula 2: ##STR00087## and Ar.sub.2 is represented by the
following Chemical Formula 3: ##STR00088## wherein: each of
Ar.sub.3 to Ar.sub.7 is independently a substituted or
unsubstituted C3 to C30 aryl group, and at least one of Ar.sub.3 to
Ar.sub.7 represents a substituted or unsubstituted C8 to C30 aryl
group, each of R.sub.1 to R.sub.5 is independently selected from
the group consisting of hydrogen, deuterium, substituted or
unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to
C30 cycloalkyl, substituted or unsubstituted C6 to C30 aryl, and
substituted or unsubstituted C2 to C30 heteroaryl, and each of k, l
and m is independently an integer of 0 to 4.
2. The compound of claim 1, wherein each of Ar.sub.3 to Ar.sub.7 is
independently a substituted or unsubstituted C8 to C30 condensed
polycyclic group.
3. The compound of claim 1, wherein each of Ar.sub.3 to Ar.sub.7 is
independently substituted or unsubstituted naphthylene, substituted
or unsubstituted phenanthrene, substituted or unsubstituted
anthracene, or substituted or unsubstituted pyrene.
4. An organic electroluminescent device, comprising: a first
electrode; a second electrode; and at least one organic layer
between the first electrode and the second electrode, the at least
one organic layer including a light emission layer, and a hole
transport layer and a hole transport auxiliary layer between the
first electrode and the light emission layer, wherein the hole
transport auxiliary layer includes a compound represented by the
following Chemical Formula 1: ##STR00089## Ar.sub.1 is represented
by the following Chemical Formula 2: ##STR00090## and Ar.sub.2 is
represented by the following Chemical Formula 3: ##STR00091##
wherein: each of Ar.sub.3 to Ar.sub.7 is independently a
substituted or unsubstituted C3 to C30 aryl group, and at least one
of Ar.sub.3 to Ar.sub.7 represents a substituted or unsubstituted
C8 to C30 aryl group, each of R.sub.1 to R.sub.5 is independently
selected from the group consisting of hydrogen, deuterium,
substituted or unsubstituted C1 to C30 alkyl, substituted or
unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C6
to C30 aryl, and substituted or unsubstituted C2 to C30 heteroaryl,
and each of k, l and m is independently an integer of 0 to 4.
5. The organic electroluminescent device of claim 4, wherein the at
least one organic layer further includes at least one layer
selected from the group consisting of a hole injection layer, an
electron transport auxiliary layer, an electrode transport layer
and an electron injection layer.
6. The organic electroluminescent device of claim 5, further
comprising a first passivation film on the second electrode, and a
second passivation film on the first passivation film.
7. The organic electroluminescent device of claim 6, wherein the
first passivation film is over an entirety of the at least one
organic layer and the second electrode.
8. The organic electroluminescent device of claim 6, further
comprising an encapsulation film on the second passivation film,
wherein the encapsulation film is bonded to the second passivation
film via an adhesive film.
9. The organic electroluminescent device of claim 5, further
comprising a driving thin film transistor including an active layer
electrically connected to the first electrode.
10. The organic electroluminescent device of claim 9, wherein the
active layer includes an oxide semiconductor material.
11. The organic electroluminescent device of claim 9, wherein the
driving thin film transistor includes: a gate insulating film on
the active layer; and a gate electrode on the gate insulating
film.
12. The organic electroluminescent device of claim 4, wherein each
of Ar.sub.3 to Ar.sub.7 is independently a substituted or
unsubstituted C8 to C30 condensed polycyclic group.
13. The organic electroluminescent device of claim 4, wherein each
of Ar.sub.3 to Ar.sub.7 is independently substituted or
unsubstituted naphthylene, substituted or unsubstituted
phenanthrene, substituted or unsubstituted anthracene, or
substituted or unsubstituted pyrene.
Description
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application claims the priority of Korean Patent
Application No. 10-2018-0134472 filed on Nov. 5, 2018 and Korean
Patent Application No. 10-2019-0126903 filed on Oct. 14, 2019 in
the Korean Intellectual Property Office, the disclosures of which
are hereby incorporated by reference in their entirety.
BACKGROUND
Technical Field
[0002] The present disclosure relates to a novel organic compound
and an organic electroluminescent device including the same.
Description of the Related Art
[0003] Recently, as a size of a display device increases, interest
in a flat panel display device having a small space occupation is
increasing. As one of the flat panel display devices, an organic
light emitting display device including an organic
electroluminescent device (organic light emitting diode: OLED) is
rapidly developing.
[0004] In the organic light emitting diode, electrons and holes are
paired to form excitons when charges are injected into a light
emitting layer formed between a first electrode and a second
electrode. Thus, energy of the excitons may be converted to light.
The organic light emitting diode may be driven at a lower voltage
and consume less power than the conventional display technology.
The organic light emitting diode may render excellent color. A
flexible substrate may be applied to the organic light emitting
diode which may have various applications.
BRIEF SUMMARY
[0005] One purpose of the present disclosure is to provide an
organic electroluminescent device with lowered driving voltage, and
enhanced efficiency and lifetime.
[0006] Purposes of the present disclosure are not limited to the
above-mentioned purpose. Other purposes and advantages of the
present disclosure which are not mentioned above may be understood
from following descriptions and more clearly understood from
embodiments of the present disclosure. Further, it will be readily
appreciated that the purposes and advantages of the present
disclosure may be realized by features and combinations thereof as
disclosed in the claims.
[0007] A novel compound according to one embodiment of the present
disclosure is represented by the following Chemical Formula 1:
##STR00001##
[0008] In the Chemical Formula 1, Ar.sub.1 is represented by the
following Chemical Formula 2:
##STR00002##
[0009] Ar.sub.2 is represented by a following Chemical Formula
3:
##STR00003##
[0010] Each of Ar.sub.3 to Ar.sub.7 independently represents a
substituted or unsubstituted C3 to C30 aryl group, and at least one
of Ar.sub.3 to Ar.sub.7 represents a substituted or unsubstituted
C8 to C30 aryl group.
[0011] Each of R.sub.1 to R.sub.5 independently represents one
selected from the group consisting of hydrogen, deuterium,
substituted or unsubstituted C1 to C30 alkyl, substituted or
unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C6
to C30 aryl, and substituted or unsubstituted C2 to C30
heteroaryl.
[0012] Each of k, l and m independently denotes an integer of 0 to
4. When k is 2 to 4, each of a plurality of R.sub.1 is
independently defined as described above, and the plurality of
R.sub.1 are the same as or different from each other. When l is 2
to 4, each of a plurality of R.sub.2 is independently defined as
described above and the plurality of R.sub.2 are the same as or
different from each other. When m is 2 to 4, each of a plurality of
R.sub.3 is independently defined as described above and the
plurality of R.sub.3 are the same as or different from each
other.
[0013] An organic electroluminescent device according to one
embodiment of the present disclosure may include a first electrode,
a second electrode, and an organic layer formed between the first
electrode and the second electrode. The organic layer includes a
light emission layer. The organic layer includes a hole transport
layer and a hole transport auxiliary layer between the first
electrode and the light emission layer. The hole transport
auxiliary layer contains the compound represented by the above
Chemical Formula 1.
[0014] Effects of the present disclosure are as follows but are not
limited thereto.
[0015] In accordance with the present disclosure, an organic
electroluminescent device with lowered driving voltage, and
enhanced efficiency and lifetime may be realized.
[0016] In addition to the effects as described above, specific
effects of the present disclosure are described together with
specific details for carrying out the present disclosure.
BRIEF DESCRIPTION OF THE SEVERAL VIEWS OF THE DRAWINGS
[0017] FIG. 1 is a schematic cross-sectional view of an organic
electroluminescent device containing a compound represented by
Chemical Formula 1 according to one embodiment of the present
disclosure.
[0018] FIG. 2 is a schematic cross-sectional view of an organic
light emitting display device including an organic
electroluminescent device according to one embodiment of the
present disclosure.
DETAILED DESCRIPTION
[0019] For simplicity and clarity of illustration, elements in the
figures are not necessarily drawn to scale. The same reference
numbers in different figures denote the same or similar elements,
and as such perform similar functionality. Furthermore, in the
following detailed description of the present disclosure, numerous
specific details are set forth in order to provide a thorough
understanding of the present disclosure. In other instances,
well-known methods, procedures, components, and circuits have not
been described in detail so as not to unnecessarily obscure aspects
of the present disclosure.
[0020] Examples of various embodiments are illustrated and
described further below. It will be understood that the description
herein is not intended to limit the claims to the specific
embodiments described. On the contrary, it is intended to cover
alternatives, modifications, and equivalents as may be included
within the spirit and scope of the present disclosure as defined by
the appended claims.
[0021] The terminology used herein is for the purpose of describing
particular embodiments only and is not intended to be limiting of
the present disclosure. As used herein, the singular forms "a" and
"an" are intended to include the plural forms as well, unless the
context clearly indicates otherwise. It will be further understood
that the terms "comprises", "comprising", "includes", and
"including" when used in this specification, specify the presence
of the stated features, integers, operations, elements, and/or
components, but do not preclude the presence or addition of one or
more other features, integers, operations, elements, components,
and/or portions thereof. As used herein, the term "and/or" includes
any and all combinations of one or more of the associated listed
items. Expression such as "at least one of" when preceding a list
of elements may modify the entire list of elements and may not
modify the individual elements of the list.
[0022] It will be understood that, although the terms "first",
"second", "third", and so on may be used herein to describe various
elements, components, regions, layers and/or sections, these
elements, components, regions, layers and/or sections should not be
limited by these terms. These terms are used to distinguish one
element, component, region, layer or section from another element,
component, region, layer or section. Thus, a first element,
component, region, layer or section described below could be termed
a second element, component, region, layer or section, without
departing from the spirit and scope of the present disclosure.
[0023] In addition, it will also be understood that when a first
element or layer is referred to as being present "on" or "beneath"
a second element or layer, the first element may be disposed
directly on or beneath the second element or may be disposed
indirectly on or beneath the second element with a third element or
layer being disposed between the first and second elements or
layers. It will be understood that when an element or layer is
referred to as being "connected to", or "coupled to" another
element or layer, it can be directly on, connected to, or coupled
to the other element or layer, or one or more intervening elements
or layers may be present. In addition, it will also be understood
that when an element or layer is referred to as being "between" two
elements or layers, it can be the only element or layer between the
two elements or layers, or one or more intervening elements or
layers may also be present.
[0024] Unless otherwise defined, all terms including technical and
scientific terms used herein have the same meaning as commonly
understood by one of ordinary skill in the art to which this
inventive concept belongs. It will be further understood that
terms, such as those defined in commonly used dictionaries, should
be interpreted as having a meaning that is consistent with their
meaning in the context of the relevant art and will not be
interpreted in an idealized or overly formal sense unless expressly
so defined herein.
[0025] As used herein, the term "unsubstituted" means that a
hydrogen atom has been substituted. In this case, the hydrogen atom
includes protium, deuterium and tritium.
[0026] As used herein, a substituent in the term "substituted" may
include one selected from the group consisting of, for example,
hydrogen, deuterium, an alkyl group of 1 to 20 carbon atoms
unsubstituted or substituted with halogen, an alkoxy group having 1
to 20 carbon atoms unsubstituted or substituted with halogen,
halogen, a cyano group, a carboxy group, a carbonyl group, an amine
group, an alkylamine group having 1 to 20 carbon atoms, a nitro
group, an alkylsilyl group having 1 to 20 carbon atoms, an
alkoxysilyl group having 1 to 20 carbon atoms, a cycloalkylsilyl
group having 3 to 30 carbon atoms, an arylsilyl group having 5 to
30 carbon atoms, an aryl group having 5 to 30 carbon atoms, an
arylamine group having 5 to 30 carbon atoms, a heteroaryl group
having 4 to 30 carbon atoms, and a combination thereof. However,
the present disclosure is not limited thereto.
[0027] As used herein, the term "hetero" as used in `hetero
aromatic ring`, `heterocycloalkylene group`, `heteroarylene group`,
`heteroaryl alkylene group`, `hetero oxy arylene group`,
`heterocycloalkyl group, `heteroaryl group, "heteroaryl alkyl
group, `hetero oxy aryl group`, and `heteroaryl amine group` means
that one or more carbon atoms, for example, 1 to 5 carbon atoms
among carbon atoms constituting the aromatic or alicyclic ring are
substituted with at least one hetero atom selected from the group
consisting of N, O, S and combinations thereof.
[0028] As used herein, the phase "combinations thereof" as used in
the definition of the substituent means that two or more
substituents are bonded to each other via a linking group or two or
more substituents are bonded to each other via condensation, unless
otherwise defined.
[0029] Hereinafter, a novel compound and an organic
electroluminescent device containing the same according to some
embodiments of the present disclosure will be described.
[0030] According to one embodiment of the present disclosure, there
is provided a novel compound represented by the following Chemical
Formula 1:
##STR00004##
[0031] In the Chemical Formula 1, Ar.sub.1 is represented by the
following Chemical Formula 2:
##STR00005##
[0032] Ar.sub.2 is represented by the following Chemical Formula
3:
##STR00006##
[0033] Each of Ar.sub.3 to Ar.sub.7 independently represents a
substituted or unsubstituted C3 to C30 aryl group, and at least one
of Ar.sub.3 to Ar.sub.7 represents a substituted or unsubstituted
C8 to C30 aryl group.
[0034] Each of R.sub.1 to R.sub.5 independently represents one
selected from the group consisting of hydrogen, deuterium,
substituted or unsubstituted C1 to C30 alkyl, substituted or
unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C6
to C30 aryl, and substituted or unsubstituted C2 to C30
heteroaryl.
[0035] Each of k, l and m independently denotes an integer of 0 to
4. When k is 2 to 4, each of a plurality of R.sub.1 is
independently defined as described above, and the plurality of
R.sub.1 are the same as or different from each other. When l is 2
to 4, each of a plurality of R.sub.2 is independently defined as
described above and the plurality of R.sub.2 are the same as or
different from each other. When m is 2 to 4, each of a plurality of
R.sub.3 is independently defined as described above and the
plurality of R.sub.3 are the same as or different from each
other.
[0036] In one embodiment, each of Ar.sub.3 to Ar.sub.7
independently represents a substituted or unsubstituted C8 to C30
condensed polycyclic group.
[0037] In one embodiment, each of Ar.sub.3 to Ar.sub.7
independently represents substituted or unsubstituted naphthylene,
substituted or unsubstituted phenanthrene, substituted or
unsubstituted anthracene, or substituted or unsubstituted
pyrene.
[0038] Specifically, a compound represented by the above Chemical
Formula 1 may be represented by one of the following compounds.
However, the present disclosure is not limited thereto.
##STR00007## ##STR00008## ##STR00009## ##STR00010## ##STR00011##
##STR00012## ##STR00013## ##STR00014## ##STR00015## ##STR00016##
##STR00017## ##STR00018## ##STR00019## ##STR00020## ##STR00021##
##STR00022## ##STR00023## ##STR00024## ##STR00025## ##STR00026##
##STR00027## ##STR00028## ##STR00029## ##STR00030## ##STR00031##
##STR00032## ##STR00033## ##STR00034## ##STR00035## ##STR00036##
##STR00037## ##STR00038## ##STR00039## ##STR00040## ##STR00041##
##STR00042## ##STR00043## ##STR00044## ##STR00045## ##STR00046##
##STR00047## ##STR00048## ##STR00049## ##STR00050## ##STR00051##
##STR00052## ##STR00053## ##STR00054## ##STR00055##
##STR00056##
[0039] The organic electroluminescent device may include an organic
layer containing a compound represented by Chemical Formula 1, as
described above.
[0040] Specifically, the organic layer may include a hole transport
layer or a hole transport auxiliary layer and may contain a
compound represented by Chemical Formula 1.
[0041] The organic layer may include at least one selected from the
group consisting of a hole injection layer, a hole transport layer,
a hole transport auxiliary layer, an electron transport auxiliary
layer, an electron transport layer and an electron injection layer,
in addition to an organic layer containing a compound represented
by Chemical Formula 1.
[0042] In one embodiment, the organic electroluminescent device may
include a hole transport auxiliary layer containing a compound
represented by Chemical Formula 1.
[0043] FIG. 1 illustrates an organic electroluminescent device 10
according to one embodiment of the present disclosure. In FIG. 1,
the organic electroluminescent device 10 may sequentially include
an anode 1, a hole injection layer 2, a hole transport layer 3, a
hole transport auxiliary layer 7, a light emission layer 4, an
electron transport layer 5, and a cathode 6.
[0044] The anode 1 provides holes into the light emission layer 4.
The anode 1 may include a conductive material having a high work
function to easily provide holes. When the organic
electroluminescent device 10 is applied to as a bottom emission
type organic light emitting display, the anode 1 may be embodied as
a transparent electrode made of a transparent conductive material.
When the organic electroluminescent device is applied to as a top
emission type organic light emitting display, the anode 1 may have
a multilayer structure in which a transparent electrode layer made
of a transparent conductive material and a reflective layer are
stacked vertically.
[0045] The cathode 6 provides electrons into the light emission
layer 4. The cathode 6 may include a conductive material having a
low work function to easily provide electrons. When the organic
electroluminescent device is applied to as a bottom emission type
organic light emitting display, the cathode 6 may be embodied as a
reflective electrode made of a metal. When the organic
electroluminescent device is applied to as a top emission type
organic light emitting display, the cathode 6 may be embodied as a
transmissive electrode made of a thin metal.
[0046] The light emission layer 4 may emit red (R), green (G), or
blue (B) light, and may be made of a phosphor or a fluorescent
material.
[0047] When the light emission layer 4 emits red light, the light
emission layer 4 may contain a host material including CBP
(carbazole biphenyl) or mCP (1,3-bis(carbazol-9-yl)). The light
emission layer 4 may contain a phosphor dopant including one
selected from the group consisting of PIQIr(acac)
(bis(1-phenylisoquinoline)acetylacetonate iridium), PQIr(acac)
(bis(1-phenylquinoline)acetylacetonate iridium), PQIr
(tris(1-phenylquinoline)iridium), PtOEP (octaethylporphyrin
platinum), and combinations thereof. Alternatively, the light
emission layer 4 may contain a fluorescent material including
PBD:Eu(DBM)3(Phen) or perylene. However, the present disclosure is
not limited thereto.
[0048] When the light emission layer 4 emits green light, the light
emission layer 4 may contain a host material including CBP or mCP.
The light emission layer 4 may contain a phosphor including a
dopant material including Ir(ppy)3 (fac tris (2-phenylpyridine)
iridium). Alternatively, the light emission layer 4 may contain a
fluorescent material including Alq3 (tris (8-hydroxyquinolino)
aluminum). However, the present disclosure is not limited
thereto.
[0049] When the light emission layer 4 emits blue light, the light
emission layer 4 may contain a host material including CBP or mCP,
and may contain a phosphor dopant including (4,6-F2ppy)2Irpic.
Alternatively, the light emission layer 4 may contain a fluorescent
material including one selected from the group consisting of
spiro-DPVBi, spiro-6P, distilbenzene (DSB), distriarylene (DSA),
PFO-based polymer and PPV-based polymer, and combinations thereof.
Alternatively, the light emission layer 4 may contain a compound of
Chemical Formula 1 as a blue fluorescent material. However, the
present disclosure is not limited thereto.
[0050] The hole injection layer 2 may serve to facilitate the
injection of holes. The hole injection layer 2 may include one or
more selected from the group consisting of, for example, cupper
phthalocyanine (CuPc), poly(3,4)-ethylenedioxythiophene (PEDOT),
polyaniline (PANI), N,N-dinaphthyl-N,N'-diphenyl benzidine (NPD)
and combinations thereof. However, the present disclosure is not
limited thereto.
[0051] The hole transport layer 3 may contain a material
electrochemically stabilized via cationization (i.e., loss of
electrons) as a hole transport material. Alternatively, a material
that produces a stable radical cation may be a hole transport
material. The hole transport layer 3 may contain a compound
represented by Chemical Formula 1. Detailed descriptions of the
compound represented by Chemical Formula 1 are as described
above.
[0052] The hole transport layer 3 may further contain an additional
hole transport material.
[0053] The additional hole transport material may be a material
containing an aromatic amine and thus being easily to be
cationized. For example, the additional hole transport material may
include one selected from the group consisting of NPD
(N,N-dinaphthyl-N,N'-diphenylbenzidine), TPD
(N,N'-bis-(3-methylphenyl)-N,N'-bis-(phenyl)-benzidine), spiro-TAD
(2,2',7,7'-tetrakis(N,N-dimethylamino)-9,9-spirofluorene), MTDATA
(4,4',4-Tris(N-3-methylphenyl-N-phenylamino)-triphenylamine), and
combinations thereof. However, the present disclosure is not
limited thereto.
[0054] The hole transport auxiliary layer 7 may contain a compound
represented by Chemical Formula 1. Detailed descriptions of the
compound represented by Chemical Formula 1 are as described
above.
[0055] The hole transport auxiliary layer 7 may further contain an
additional hole transport auxiliary material other than the
compound represented by Chemical Formula 1.
[0056] The additional hole transport auxiliary material may include
one selected from the group consisting of TCTA
(tris[4-(diethylamino)phenyl]amine),
N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-
-fluoren-2-amine, tri-p-tolylamine, TAPC
(1,1-bis(4-(N,N'-di(ptolyl)amino)phenyl)cyclohexane), MTDATA, mCP,
mCBP, CuPC, DNTPD
(N,N'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N,N'-diphenyl-[1,1'-bipheny-
l]-4,4'-diamine), TDAPB, and combinations thereof. However, the
present disclosure is not limited thereto.
[0057] The electron transport auxiliary layer 8 may be located
between the electron transport layer 5 and the light emission layer
4. The electron transport auxiliary layer 8 may further contain a
hole blocking material.
[0058] The hole blocking material may include one selected from the
group consisting of, for example, oxadiazole, triazole,
phenanthroline, benzoxazole, benzothiazole, benzimidazole,
triazine, and a combination thereof. However, the present
disclosure is not limited thereto.
[0059] The electron transport layer 5 receives electrons from the
cathode. The electron transport layer 5 transfers the supplied
electrons to the light emission layer 4.
[0060] The electron transport layer 5 serves to facilitate the
transport of electrons, and the electron transport layer 5 may
contain an electron transport material.
[0061] The electron transport material may be a material
electrochemically stabilized via anionization (that is, via
obtaining electrons). Alternatively, a material producing stable
radical anions may be an electron transport material.
Alternatively, a material including a heterocyclic ring and thus
being easily to be anionized using a hetero atom may be an electron
transport material.
[0062] For example, the electron transport material may include one
selected from the group consisting of PBD
(2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4oxadiazole), TAZ
(3-(4-biphenyl)4-phenyl-5-tert-butylphenyl-1,2,4-triazole),
spiro-PBD, TPBi
(2,2',2-(1,3,5-benzinetriyl)-tris(1-phenyl-1-H-benzimidazole),
oxadiazole, triazole, phenanthroline, benzoxazole, benzthiazole,
and combinations thereof. However, the present disclosure is not
limited thereto.
[0063] For example, the electron transport material may be an
organometallic compound. Specifically, the electron transport
material may include an organoaluminum compound or organolithium
compound such as Alq3 (tris(8-hydroxyquinolino)aluminum), Liq
(8-hydroxyquinolinolatolithium), BAlq
(bis(2-methyl-8-quinolinolate)-4-(phenylphenolato)aluminium), and
SAlq. However, the present disclosure is not limited thereto.
[0064] Specifically, the organometallic compound may be an
organolithium compound.
[0065] More specifically, a ligand bound to lithium of the
organolithium compound may be a hydroxyquinoline based ligand.
[0066] The organic layer may further include an electron injection
layer.
[0067] The electron injection layer serves to facilitate the
injection of electrons. The electron injection material may include
one selected from the group consisting of Alq3
(tris(8-hydroxyquinolino)aluminum), PBD. TAZ, spiro-PBD, BAlq,
SAlq, and a combination thereof. However, the present disclosure is
not limited thereto. Alternatively, the electron injection layer
may be made of a metal compound. The metal compound may include,
for example, at least one selected from the group consisting of
LiQ, LiF, NaF, KF, RbF, CsF, FrF, BeF.sub.2, MgF.sub.2, CaF.sub.2,
SrF.sub.2, BaF.sub.2 and RaF.sub.2. However, the present disclosure
is not limited thereto.
[0068] The organic layer may further include one selected from the
group consisting of a hole injection layer, a hole transport layer,
a hole transport auxiliary layer, an electron transport auxiliary
layer, an electron injection layer, and combinations thereof in
addition to the electron transport layer. Each of the hole
injection layer, the hole transport layer, the hole transport
auxiliary layer, the electron transport auxiliary layer, the
electron transport layer and the electron injection layer may be
formed of a single layer or a stack of a plurality of layers.
[0069] An organic electroluminescent device according to the
present disclosure may be applied to an organic light emitting
display such as a mobile device and TV. For example, FIG. 2 is a
schematic cross-sectional view of an organic light emitting display
3000 according to an exemplary embodiment of the present
disclosure.
[0070] As shown in FIG. 2, the organic light emitting display 3000
may include a substrate 3010, an organic electroluminescent device
4000, and an encapsulation film 3900 covering the organic
electroluminescent device 4000. A driving thin film transistor Td
as a driving element, and the organic electroluminescent device
4000 connected to the driving thin film transistor Td are
positioned on the substrate 3010.
[0071] Although not shown, following components are disposed on the
substrate 3010: a gate line, and a data line crossing each other to
define a pixel region, a power line extending in parallel with and
spaced from one of the gate line and the data line, a switching
thin film transistor connected to the power line and the gate line,
and a storage capacitor connected to one electrode of the switching
thin film transistor and the power line.
[0072] The driving thin film transistor Td is connected to the
switching thin film transistor, and includes a semiconductor layer
3100, a gate electrode 3340, a source electrode 3520, and a drain
electrode 3540.
[0073] The semiconductor layer 3100 is formed on the substrate 3010
and may be made of an oxide semiconductor material, polycrystalline
silicon, an alloy of molybdenum titanium (MoTi), or the like. When
the semiconductor layer 3100 is made of an oxide semiconductor
material, a light blocking pattern (not shown) may be formed below
the semiconductor layer 3100. The light blocking pattern prevents
light from entering the semiconductor layer 3100 to prevent the
semiconductor layer 3100 from being degraded by light.
Alternatively, the semiconductor layer 3100 may be made of
polycrystalline silicon. In this case, impurities may be doped into
both edges of the semiconductor layer 3100.
[0074] A buffer layer 3200 made of an insulating material is formed
on the semiconductor layer 3100 over an entire face of the
substrate 3010. The buffer layer 3200 may be made of an inorganic
insulating material such as silicon oxide or silicon nitride.
[0075] The active layer 3300 made of a conductive material such as
a metal is formed on the buffer layer 3200 in a position
corresponding to a center region of the semiconductor layer 3100.
The active layer 3300 may be made of an oxide semiconductor layer.
For example, the active layer 3300 may be made of an amorphous
semiconductor of indium, gallium and zinc oxide (IGZO).
[0076] The gate electrode 3340 is formed on the active layer 3300
while a gate insulating layer 3320 is interposed therebetween. The
gate insulating layer 3320 may be made of, for example, silicon
oxide. The gate electrode 3340 formed of, for example, a double
metal layer of a Cu film and a MoTi alloy film may be formed on the
gate insulating layer 3320.
[0077] An interlayer insulating layer 3400 made of an insulating
material is formed on the active layer 3300 and the gate electrode
3340 as positioned on the buffer layer 3200 over the entire face of
the substrate 3010. The interlayer insulating layer 3400 may be
made of an inorganic insulating material such as silicon oxide or
silicon nitride, or may be made of an organic insulating material
such as benzocyclobutene or photo-acryl.
[0078] The interlayer insulating layer 3400 has first and second
active layer contact holes 3420 and 3440 defined therein exposing
both sides of the active layer 3300 respectively. The first and
second active layer contact holes 3420 and 3440 are positioned
adjacent to both sides of the gate electrode 3340 respectively and
are spaced apart from the gate electrode 3340.
[0079] The source electrode 3520 and the drain electrode 3540 made
of a conductive material such as metal are formed on the interlayer
insulating layer 3400. The source electrode 3520 and the drain
electrode 3540 are spaced apart from each other while the gate
electrode 3340 is positioned therebetween. The source electrode
3520 and the drain electrode 3540 contact both sides of the active
layer 3300 respectively via the first and second active layer
contact holes 3420 and 3440 respectively. The source electrode 3520
is connected to the power line (not shown).
[0080] The semiconductor layer 3100, the active layer 3300, the
gate electrode 3340, the source electrode 3520, and the drain
electrode 3540 may form the driving thin film transistor Td. The
driving thin film transistor Td may have a coplanar structure in
which the gate electrode 3340, the source electrode 3520, and the
drain electrode 3540 are positioned above the semiconductor layer
3100.
[0081] In contrast, the driving thin film transistor Td may have an
inverted staggered structure in which the gate electrode is
disposed under the semiconductor layer, while the source electrode
and the drain electrode are positioned above the semiconductor
layer. In this case, the semiconductor layer may be made of
amorphous silicon. The switching thin film transistor (not shown)
may have a structure substantially the same as that of the driving
thin film transistor Td.
[0082] An insulating film 3500 having a drain contact hole 3720
defined therein exposing the drain electrode 3540 of the driving
thin film transistor Td may be formed to cover the driving thin
film transistor Td. The insulating film 3500 may be made of an
inorganic insulating material or an organic insulating
material.
[0083] In one embodiment, the organic light emitting display 3000
may include a color filter 3600 that absorbs light generated from
the organic electroluminescent device 4000. For example, the color
filter 3600 may absorb red (R), green (G), blue (B), and white (W)
light. In this case, red, green, and blue color filter patterns for
absorbing light may be formed separately on corresponding pixel
areas respectively. A corresponding color filter pattern may
overlap an organic layer 4300 of an organic electroluminescent
device that emits light of a corresponding wavelength band to be
absorbed. Adopting the color filter 3600 may allow the organic
light emitting display 3000 to implement full color.
[0084] For example, when the organic light emitting display 3000 is
of a bottom emission type, the color filter 3600 may be disposed
above the insulating film 3500 in a corresponding position to the
corresponding organic electroluminescent device 4000. In an
alternative embodiment, when the organic light emitting display
3000 is of the top emission type, the color filter 3600 may be
positioned above the corresponding organic electroluminescent
device 4000, that is, above the second electrode 4200. In one
embodiment, the color filter 3600 may be formed to a thickness of
about 2 .mu.m to about 5 .mu.m. In this case, the organic
electroluminescent device 4000 may have the structure shown in FIG.
1.
[0085] An overcoat layer 3700 is formed to cover the color filter
3600 formed on the insulating layer 3500. The overcoat layer 3700
may be made of an organic material such as photoacryl (PAC).
[0086] The first electrode 4100 is formed on the overcoat layer
3700. The first electrode 4100 is patterned with a bank layer 3800
to corresponding to each pixel region. The first electrode 4100 is
connected to the drain electrode 3540 of the driving thin film
transistor Td via the drain contact hole 3720 penetrating the
insulating film 3500 and the overcoat layer 3700. Accordingly, the
active layer 3300 of the driving thin film transistor Td is
electrically connected to the first electrode 4100.
[0087] The first electrode 4100 may be an anode and may be made of
a conductive material having a relatively large work function
value. For example, the first electrode 410 may be made of a
transparent conductive material such as of ITO, IZO or ZnO.
[0088] In one embodiment, when the organic light emitting display
3000 is of a top emission type, a reflective electrode or a
reflective layer may be further formed below the first electrode
4100. For example, the reflective electrode or the reflective layer
may be made of one of aluminum (Al), silver (Ag), nickel (Ni), and
aluminum-palladium-copper (APC) alloy.
[0089] The bank layer 3800 is formed on the overcoat layer 3700 to
cover edges of the first electrode 4100 and the overcoat layer
3700. The bank layer 3800 exposes a central region of the first
electrode 4100 corresponding to each pixel region.
[0090] The organic layer 4300 is formed on the first electrode
4100.
[0091] The second electrode 4200 is formed on the organic layer
4300. The second electrode 4200 may be disposed in the entirety of
a display area and may be used as a cathode and may be made of a
conductive material having a relatively small work function. For
example, the second electrode 4200 may be made of one of aluminum
(Al), magnesium (Mg), and aluminum-magnesium alloy (AlMg).
[0092] The first electrode 4100, the organic layer 4300, and the
second electrode 4200 form the organic electroluminescent device
4000.
[0093] A first passivation layer 4400 and a second passivation
layer 4500 are sequentially stacked on the second electrode 4200.
As shown in FIG. 2, the first passivation layer 4400 may be formed
on an entirety of the second electrode 4200. Then, the second
passivation layer 4500 may be formed on the first passivation layer
4400. Thus, moisture, hydrogen, and oxygen may be prevented from
penetrating into the organic layer 4300 and the second electrode
4200. That is, the first passivation layer 4400 is formed on the
second electrode 4200 to prevent the organic layer 4300 and the
second electrode 4200 from being damaged by moisture, oxygen, or
the like, or thus from having deteriorated light emission
characteristics. For example, the first passivation layer 4400 may
be made of an anthracene-based compound, Alq3, or the like.
[0094] The first passivation layer 4400 may be deposited on the
second electrode 4200 uniformly and evenly. Since the first
passivation layer 4400 is uniformly and evenly deposited, the
second passivation layer 4500 is also uniformly deposited on the
first passivation layer 4400. As such, the first and second
protective layers 4400 and 4500 that are evenly and uniformly
formed may prevent penetration of water or oxygen into the organic
electroluminescent device 4000, such that the lifetime of the
organic electroluminescent device 4000 can be improved.
[0095] The second passivation layer 4500 may be formed between the
organic electroluminescent device 4000 and an adhesive film 4600 to
prevent the organic electroluminescent device 4000 from being
damaged by moisture, oxygen, or the like, or from having
deteriorated light emission characteristics. The second passivation
layer 4500 is formed to be in contact with the adhesive film 4600,
thereby preventing moisture, hydrogen, oxygen, and the like from
flowing into the organic electroluminescent device 4000. The second
passivation layer 4500 may be made of an inorganic insulating layer
such as silicon nitride, silicon oxide, or silicon oxynitride.
[0096] The adhesive film 4600 may be formed on the second
passivation layer 4500. In this connection, in order to prevent
external moisture from penetrating into the organic
electroluminescent device 4000, an encapsulation film 3900 may be
formed on the adhesive film 4600. That is, the encapsulation film
3900 is formed on the second passivation layer 4500. The
encapsulation film 3900 may adhere to the second passivation layer
4500 via the adhesive film 4600.
[0097] After the adhesive film 4600 is applied to a front face of
the second passivation layer 4500 or a back face of the
encapsulation film 3900, the encapsulation film 3900 may adhere to
the substrate 3010 on which the organic electroluminescent device
4000 is formed via the adhesive film 4600.
[0098] The adhesive film 4600 may be made of, for example, an epoxy
adhesive.
[0099] The encapsulation film 3900 may be embodied as, for example,
a double metal layer of a Fe film and a Ni film. Alternatively, the
encapsulation film 3900 may be embodied as a triple layer structure
(not shown) in which a first inorganic layer, an organic layer, and
a second inorganic layer are sequentially stacked vertically.
However, the present disclosure is not limited thereto.
[0100] Hereinafter, Examples and Comparative Examples of the
present disclosure are described. The Present Examples are merely
examples of the present disclosure. The present disclosure is not
limited to the Present Examples as described below.
EXAMPLES
[0101] Hereinafter, compounds used in the Present Examples and
Comparative Examples were synthesized as follows.
Synthesis Example 1
Preparation of Compound 1
1-A) Preparation of Intermediate 1-A
##STR00057##
[0103] Under nitrogen stream, 9-(4-bromophenyl)-9H-carbazole (50.0
g, 155.2 mmol), [1,1': 4',1''-terphenyl]-4-amine (41.88 g, 170.7
mmol), sodium tert butoxide (29.83 g, 310.4 mmol),
tris(dibenzylideneacetone)dipalladium (0) (2.84 g, 3.10 mmol),
2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (2.55 g, 6.21
mmol), and toluene 800 mL were added into a 2000 mL flask and were
stirred therein while being refluxed. After completion of the
reaction, a toluene layer was extracted using 500 mL of water. An
extracted solution was treated with MgSO.sub.4 to remove residual
water, and concentrated under reduced pressure, and purified using
column chromatography. The resulting solid is subjected to
recrystallization using dichloromethane/heptane, thereby obtaining
57.10 g of an intermediate 1-A in 75.6% yield.
1-B) Preparation of Compound 1
##STR00058##
[0105] Under nitrogen stream,
N-(4-(9H-carbazol-9-yl)phenyl)-[1,1':4',1''-terphenyl]-4-amine (8.0
g, 16.44 mmol), 1-(4-bromophenyl)naphthalene (5.12 g, 18.08 mmol),
sodium tert butoxide (3.16 g, 32.88 mmol),
tris(dibenzylideneacetone)dipalladium (0) (0.30 g, 0.33 mmol),
2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.27 g, 0.66
mmol), and 100 mL of toluene were added into a 250 mL flask and
were stirred therein while being refluxed. After completion of the
reaction, a toluene layer was extracted using 50 mL of water. An
extracted solution was treated with MgSO.sub.4 to remove residual
water, and concentrated under reduced pressure, and purified using
column chromatography. The resulting solid is subjected to
recrystallization using dichloromethane/heptane, thereby obtaining
6.85 g of Compound 1 in 60.5% yield.
[0106] MS (MALDI-TOF) m/z: 688 [M]+
Synthesis Example 2
Preparation of Compound 2
##STR00059##
[0108] 6.07 g of Compound 2 is synthesized at 53.6% yield in the
same manner as in the preparation of Compound 1, except that
2-(4-bromophenyl)naphthalene (5.12 g, 18.08 mmol) was used instead
of 1-(4-bromophenyl)naphthalene.
[0109] MS (MALDI-TOF) m/z: 688 [M]+
Synthesis Example 3
Preparation of Compound 3
3-A) Preparation of Intermediate 3-A
##STR00060##
[0111] Under nitrogen stream, 9-bromophenanthrene (40.0 g, 155.6
mmol), (4-chlorophenyl)boronic acid (26.76 g, 171.1 mmol),
potassium carbonate (43.0 g, 311.1 mmol),
tetrakis(triphenylphosphine)palladium (0) (5.39 g, 4.67 mmol),
toluene (300 mL), EtOH (100 mL) and H.sub.2O (100 mL) were added
into a 1000 mL flask and were stirred therein while being refluxed.
After completion of the reaction, a toluene layer was extracted
using toluene and water. An extracted solution was treated with
MgSO.sub.4 to remove residual water, and concentrated under reduced
pressure, and purified using column chromatography. The resulting
solid is subjected to recrystallization using
dichloromethane/heptane, thereby obtaining 38.5 g of an
intermediate 3-A in 85.7% yield.
3-B) Preparation of Compound 3
##STR00061##
[0113] 6.37 g of Compound 3 was synthesized at 52.4% yield in the
same manner as the preparation of Compound 1, except that
9-(4-chlorophenyl)phenanthrene (5.22 g, 18.08 mmol) was used
instead of l-(4-bromophenyl) naphthalene.
[0114] MS (MALDI-TOF) m/z: 738 [M]+
Synthesis Example 4
Preparation Op Compound 4
4-A) Preparation of Intermediate 4-A
##STR00062##
[0116] 17.40 g of an intermediate 4-A was synthesized at 68.1 yield
in the same manner as the preparation of the intermediate 3-A,
except for using phenylboronic acid (12.0 g, 90.22 mmol) and
1,4-dibromonaphthalene (28.38 g, 99.24 mmol).
4-B) Preparation of Compound 4
##STR00063##
[0118] 6.01 g of Compound 2 was synthesized at 55.8% yield in the
same manner as in the preparation of Compound 1, except that
1-bromo-4-phenylnaphthalene (5.12 g, 18.80 mmol) was used instead
of 1-(4-bromophenyl)naphthalene.
[0119] MS (MALDI-TOF) m/z: 688 [M]+
Synthesis Example 5
Preparation of Compound 11
5-A) Preparation of Intermediate 5-A
##STR00064##
[0121] 45.10 g of an intermediate 5-A was synthesized at 63.1%
yield in the same manner as in the preparation of the intermediate
1-A, except using 4-(naphthalen-1-yl)aniline (37.43 g, 170.7 mmol)
instead of [1,1': 4',1''-terphenyl]-4-amine.
5-B) Preparation of Intermediate 5-B
##STR00065##
[0123] 11.85 g of an intermediate 5-B was produced at 72.7% yield
in the same manner as the preparation of the intermediate 3-A
except for using 1-bromo-4-methylbenzene (10.0 g, 58.47 mmol) and
(4'-chloro-[1,1'-biphenyl]-4-yl)boronic acid (14.95 g, 64.31
mmol).
5-C) Preparation of Compound 11
##STR00066##
[0125] 5.44 g of Compound 11 was produced at a yield of 50.9% in
the same manner as in the preparation of Compound 1, except that
N-(4-(9H-carbazol-9-yl)phenyl)-4-(naphthalen-1-yl)aniline (7.0 g,
15.20 mmol) and 4-chloro-4''-methyl-1,1':4',1''-terphenyl (4.66 g,
16.72 mmol).
[0126] MS (MALDI-TOF) m/z: 702 [M]+
Synthesis Example 6
Preparation of Compound 15
6-A) Preparation of Intermediate 6-A
##STR00067##
[0128] 39.82 g of an intermediate 6-A was produced at 81.3% yield
in the same manner as the preparation of the intermediate 3-A,
except that 1-(4-bromophenyl)naphthalene (44.06 g, 155.6 mmol) was
used instead of 9-bromophenanthrene.
6-B) Preparation of Compound 15
##STR00068##
[0130] 6.21 g of Compound 15 was produced at 55.3% yield in the
same manner as the preparation of Compound 1 except that
N-(4-(9H-carbazol-9-yl)phenyl)-4-(naphthalen-1-yl)aniline (7.0 g,
15.20 mmol) and 1-(4'-chloro-[1,1'-biphenyl]-4-yl)naphthalene (5.26
g, 16.72 mmol).
[0131] MS (MALDI-TOF) m/z: 738 [M]+
Synthesis Example 7
Preparation of Compound 21
7-A) Reparation of Intermediate 7-A
##STR00069##
[0133] 49.75 g of an intermediate 7-A was obtained at 78.1% yield
in the same manner as the preparation of the intermediate 1-A,
except that [1,1'-biphenyl]-4-amine (28.89 g, 170.7 mmol) was used
instead of [1,1':4',1''-terphenyl]-4-amine.
7-B) Preparation of Compound 21
##STR00070##
[0135] 5.30 g of Compound 21 was produced at 52.6% yield in the
same manner as in the preparation of Compound 1, except that
N-(4-(9H-carbazol-9-yl)phenyl)-[1,1'-biphenyl]-4-amine (6.0 g,
14.62 mmol) and 1-(4'-chloro-[1,1'-biphenyl]-4-yl)naphthalene (5.05
g, 16.08 mmol) were used.
[0136] MS (MALDI-TOF) m/z: 688 [M]+
Synthesis Example 8
Preparation of Compound 26
8-A) Preparation of Intermediate 8-A
##STR00071##
[0138] 39.82 g of an intermediate 8-A was obtained at 81.3% yield
in the same manner as the preparation of the intermediate 3-A
except for using 2-(4-bromophenyl)naphthalene (44.06 g, 155.6 mmol)
instead of 9-bromophenanthrene.
8-B) Preparation of Compound 26
##STR00072##
[0140] 5.72 g of Compound 26 was produced at a yield of 50.9% in
the same manner as in the preparation of Compound 1 except for
using N-(4-(9H-carbazol-9-yl)phenyl)-4-(naphthalen-1-yl)aniline
(7.0 g, 15.20 mmol) and
2-(4'-chloro-[1,1'-biphenyl]-4-yl)naphthalene (5.26 g, 16.72
mmol).
[0141] MS (MALDI-TOF) m/z: 738 [M]+
Synthesis Example 9
Preparation of Compound 32
##STR00073##
[0143] 5.52 g of Compound 32 was produced at a yield of 54.8% in
the same manner as in the preparation of Compound 1 except for
using N-(4-(9H-carbazol-9-yl)phenyl)-[1,1'-biphenyl]-4-amine (6.0
g, 14.62 mmol) and 2-(4'-chloro-[1,1'-biphenyl]-4-yl)naphthalene
(5.05 g, 16.08 mmol).
[0144] MS (MALDI-TOF) m/z: 688 [M]+
Synthesis Example 10
Preparation of Compound 43
10-A) Preparation of Intermediate 10-A
##STR00074##
[0146] 43.25 g of an intermediate 10-A was produced at 76.2% yield
in the same manner as in the preparation of the intermediate 3-A
except for using (4'-chloro-[1,1'-biphenyl]-4-yl)boronic acid
(39.78 g, 171.1 mmol) instead of (4-chlorophenyl)boronic acid.
10-B) Preparation of Compound 43
##STR00075##
[0148] 5.46 g of Compound 43 was produced at 50.6% yield in the
same manner as the preparation of Compound 1 except for using
N-(4-(9H-carbazol-9-yl)phenyl)-[1,1'-biphenyl]-4-amine (6.0 g,
14.62 mmol) and 9-(4'-chloro-[1,1'-biphenyl]-4-yl)phenanthrene
(5.87 g, 16.08 mmol).
[0149] MS (MALDI-TOF) m/z: 738 [M]+
Synthesis Example 11
Preparation of Compound 48
##STR00076##
[0151] 6.48 g of Compound 48 was produced at a yield of 54.0% in
the same manner as in the preparation of Compound 1 except that
1-(4'-chloro-[1,1'-biphenyl]-4-yl) naphthalene (5.69 g, 18.08 mmol)
was used instead of 1-(4-bromophenyl)naphthalene.
[0152] MS (MALDI-TOF) m/z: 764 [M]+
Synthesis Example 12
Preparation of Compound 49
##STR00077##
[0154] Compound 49 was obtained in 8.25 g, and at 52.3% yield in
the same manner as in the preparation of Compound 1 except that
4-(9H-carbazol-9-yl)aniline (5.0 g, 19.36 mmol) and
1-(4'-chloro-[1,1'-biphenyl]-4-yl)naphthalene (13.41 g, 42.58 mmol)
were used.
[0155] MS (MALDI-TOF) m/z: 814 [M]+
Synthesis Example 13
Preparation of Compound 55
##STR00078##
[0157] Compound 55 was obtained in 7.86 g and at 49.8% yield in the
same manner as in the preparation of Compound 1 except that
4-(9H-carbazol-9-yl)aniline (5.0 g, 19.36 mmol) and
2-(4'-chloro-[1,1'-biphenyl]-4-yl)naphthalene (13.41 g, 42.58 mmol)
were used.
[0158] MS (MALDI-TOF) m/z: 814 [M]+
Synthesis Example 14
Preparation of Compound 59
##STR00079##
[0160] 6.59 g of Compound 59 was prepared at a yield of 54.0% in
the same manner as in preparation of Compound 1 except that
2-(4'-chloro-[1,1'-biphenyl]-4-yl)naphthalene (5.69 g, 18.08 mmol)
was used instead of 1-(4-bromophenyl) naphthalene.
[0161] MS (MALDI-TOF) m/z: 764 [M]+
Synthesis Example 15
Preparation of Compound 63
##STR00080##
[0163] Compound 63 was obtained in 6.87 g and at 51.3% yield in the
same manner as in the preparation of Compound 1 except for using
9-(4'-chloro-[1,1'-biphenyl]-4-yl)phenanthrene (6.60 g, 18.08 mmol)
instead of 1-(4-bromophenyl)naphthalene.
[0164] MS (MALDI-TOF) m/z: 814 [M]+
Synthesis Example 16
Preparation of Compound 118
16-A) Reparation of Intermediate 16-A
##STR00081##
[0166] 15.31 g of an intermediate 16-A was prepared at 62.0% yield
in the same manner as the preparation of the intermediate 3-A,
except that 1-naphthalene boronic acid (15.0 g, 87.21 mmol) and
1-bromo-2-iodobenzene (27.14 g, 95.94 mmol) were used.
16-B) Preparation of Intermediate 16-B
##STR00082##
[0168] 17.90 g of an intermediate 16-B was obtained at 69.5% yield
in the same manner as the preparation of the intermediate 3-A,
except for using 4-bromoaniline (15.0 g, 87.19 mmol) and
(4-(naphthalen-1-yl)phenyl)boronic acid (27.14 g, 95.91 mmol).
16-C) Preparation of Intermediate 16-C
##STR00083##
[0170] An intermediate 16-C was produced in 12.58 g and at 71.6%
yield in the same manner as in the preparation of the intermediate
1-A except for using 1-(2-bromophenyl)naphthalene (10.0 g, 35.31
mmol) and 4'-(naphthalen-1-yl)-[1,1'-biphenyl]-4-amine (11.47 g,
38.85 mmol).
16-D) Preparation of Compound 118
##STR00084##
[0172] 6.25 g of Compound 118 was produced at 52.6% yield in the
same manner as the preparation of Compound 1 except for using
4'-(naphthalen-1-yl)-N-(2-(naphthalen-1-yl)phenyl)-[1,1'-biphenyl]-4-amin-
e (8.0 g, 16.08 mmol) and 9-(4-bromophenyl)-9H-carbazole (5.70 g,
17.68 mmol).
[0173] MS (MALDI-TOF) m/z: 738 [M]+
Example 1
Organic Electroluminescent Device Preparation
[0174] An anode made of ITO was formed on a substrate on which a
reflective layer is formed. Then, the anode was subjected to
surface treatment with N.sub.2 plasma or UV-ozone. HAT-CN was
deposited on the anode to a thickness of 10 nm to form a hole
injection layer (HIL). Subsequently, a hole transport layer (HTL)
was deposited on the HIL by depositing
N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine
on the HIL to a thickness of 110 nm.
[0175] Vacuum deposition of Compound 1 on the hole transport layer
to a thickness of 10 nm was performed to form a hole transport
auxiliary layer. While depositing 25 nm of
9,10-bis(2-naphthyl)anthraces (ADN) as a blue light emission layer
(EML) on the hole transport auxiliary layer, about 3 wt % of
2,5,8,11-tetra-butyl-perylene (t-Bu-Perylene) as a dopant was doped
into the AND. Then, an anthracene derivative and LiQ were mixed
with each other at a mass ratio of 1:1 to form a mixture which in
turn was deposited on the EML to a thickness of 30 nm to form an
electron transport layer (ETL). Then, LiQ was deposited to a
thickness of 1 nm on the ETL to form an electron injection layer
(EIL). Thereafter, a mixture of magnesium and silver (Ag) in a mass
ratio of 9:1 was deposited on the EIL to a thickness of 15 nm to
form a cathode.
[0176] Then,
N4,N4'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biph-
enyl]-4,4'-diamine (DNTPD) as a capping layer was deposited to a
thickness of 60 nm on the cathode. Then, a seal cap containing a
moisture absorbent was bonded onto the capping layer with a UV
curable adhesive to protect the organic electroluminescent device
from O.sub.2 or moisture in the atmosphere. In this way, the
organic electroluminescent device was prepared.
Examples 2 to 16
[0177] Organic electroluminescent devices were prepared in the same
manner as in Example 1 except for using Compound 2 to Compound 4,
and compounds 1, 15, 21, 26, 32, 43, 48, 49, 55, 59, 63, and 118
instead of the compound 1 as the hole transport auxiliary layer in
Example 1.
Comparative Examples 1 to 3
[0178] Organic electroluminescent devices were prepared in the same
manner as in Example 1 except that NPB and following [compound A]
to [compound C] were used instead of Compound 1 as the hole
transport auxiliary layer in Example 1.
##STR00085##
Experimental Example 1
Device Performance Analysis
[0179] Electroluminescent characteristics of the organic
electroluminescent devices prepared in Examples and Comparative
Examples were analyzed under a condition of 10 mA/cm.sup.2. The
life-span characteristics were measured using a time (LT95) (hr)
consumed for a current luminance to reach 95% of an initial
luminance under a constant current driving condition of 20
mA/cm.sup.2. Results are shown in Table 1 below.
TABLE-US-00001 TABLE 1 Hole transport LT95 Examples auxiliary layer
V Cd/A Im/W CIEx CIEy (hrs) Example 1 Compound 1 3.74 6.2 5.2 0.14
0.049 195 Example 2 Compound 2 3.89 6.2 5 0.14 0.046 165 Example 3
Compound 3 3.96 6.0 4.8 0.141 0.044 175 Example 4 Compound 4 3.85
6.5 5.3 0.139 0.048 155 Example 5 Compound 11 3.9 5.3 4.2 0.14
0.049 170 Example 6 Compound 15 3.93 6.9 5.5 0.142 0.045 190
Example 7 Compound 21 3.93 6.2 5.0 0.139 0.05 165 Example 8
Compound 26 3.88 6.0 4.9 0.141 0.049 195 Example 9 Compound 32 3.91
5.9 4.7 0.14 0.045 175 Example 10 Compound 43 4.05 6.1 4.7 0.142
0.046 180 Example 11 Compound 48 3.86 6.0 4.8 0.143 0.041 170
Example 12 Compound 49 3.88 5.9 4.7 0.143 0.141 190 Example 13
Compound 55 3.79 5.9 4.9 0.142 0.045 210 Example 14 Compound 59
3.80 6.2 5.1 0.14 0.046 175 Example 15 Compound 63 4.0 6.0 4.7
0.141 0.044 170 Example 16 Compound 118 3.95 6.0 4.8 0.143 0.041
150 Comparative NPB 4.21 5.6 4.2 0.139 0.05 80 Example 1
Comparative Compound A 3.88 5.8 4.7 0.14 0.049 96 Example 2
Comparative Compound B 4.05 5.7 4.8 0.141 0.047 120 Example 3
Comparative Compound C 3.96 6.0 4.8 0.142 0.047 125 Example 4
[0180] As evident from the above table 1, the efficiency of the
organic electroluminescent devices prepared in Examples 1 to 16
were equivalent to that of the organic electroluminescent devices
prepared in Comparative Examples 1 to 4. The lifetimes of the
organic electroluminescent devices prepared in Examples 1 to 16
were increased by about 100% compared to the lifespans of the
organic electroluminescent devices prepared in Comparative Examples
1 to 4.
[0181] As described above, the present disclosure is described with
reference to the drawings. However, the present disclosure is not
limited by the embodiments and drawings disclosed in the present
specification. It will be apparent that various modifications may
be made thereto by those skilled in the art within the scope of the
present disclosure. Furthermore, although the effect resulting from
the features of the present disclosure has not been explicitly
described in the description of the embodiments of the present
disclosure, it is obvious that a predictable effect resulting from
the features of the present disclosure should be recognized.
[0182] The various embodiments described above can be combined to
provide further embodiments. These and other changes can be made to
the embodiments in light of the above-detailed description. In
general, in the following claims, the terms used should not be
construed to limit the claims to the specific embodiments disclosed
in the specification and the claims, but should be construed to
include all possible embodiments along with the full scope of
equivalents to which such claims are entitled. Accordingly, the
claims are not limited by the disclosure.
* * * * *